Life and Career
Hylan was born in Hunter, New York a town in upstate Greene County where his family owned a farm. Hylan married young, became dissatisfied with farm life and moved to Brooklyn with his bride, and enrolled at New York Law School in Manhattan. He found work on the Brooklyn Union Elevated Railroad and rose through the ranks to become a locomotive engineer. Ambitious, he studied law even as he worked on the railroad. He was fired after allegedly taking a curve too fast, endangering a supervisor who had been preparing to cross a track. Hylan always contended that he was wrongfully discharged. (Some versions of the story have him reading his law book at the same time as driving).
He was a long-time resident of the Bushwick neighborhood of Brooklyn.
Hylan became a judge in the Kings County (Brooklyn) county court and was in that position when he was tapped by Tammany Hall as a dark-horse candidate for Mayor, running as a Democrat, through the promotion of newspaper magnate William Randolph Hearst, who shared with him a desire for municipal ownership of utilities.
Hylan defeated the reformer John Purroy Mitchel in the 1917 mayoral election, restoring the power of Tammany at City Hall. He easily won re-election in 1921 but was defeated for re-nomination in 1925 by State Senator James J. "Jimmy" Walker. Walker later appointed Hylan to the municipal judiciary.
As mayor, Hylan railed against "the interests" and put in motion the building of a publicly owned and operated subway system, which became the IND division of the New York City Subway.
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